As most of the whiskies you have are large productions from major brands, and having perused your list, I have a couple ideas.
First, pair like things and try and find differences. For example, do a night with all the Beam whiskies, or all the blended Scotch, or all the single malts, or all the Irish whiskies...
Second, take those like whiskies and add something totally unique. The smallest production whisky you have is Tobermory, but it is an official bottling from the distillery. The idea is to get into the smaller brands because I think you'll generally find more interesting whisky and better quality than the monster brands.
So, for the Beam stuff, either extend the line with Knob Creek or Baker's or add some small brand like Pure Kentucky XO, Willett Family Pot Still Reserve Bourbon, Smooth Rambler Old Scout, Kinnickinnic...
For the blended Scotch, source one of the major malt components for the blend. For Pinch that'd be a malt from Glenkinchie or Linkwood (Linkwood less available as a single so that'd be the best one to find for its uniqueness). For Chivas find Strathisla. Monkey Shoulder is a blend of Kininvie, Balvenie and Glenfiddich. All three distilleries are on the Glenfiddich property in Dufftown. Kininvie has never released a single, to my knowledge, and Balvenie and Glenfiddich are readily available and not at all rare.
For the Irish you have, definitely get off the Jameson kick. Try the single malts from either Bushmills, Michael Collins or Knappogue Castle. Redbreast pure pot still would be another very interesting whisky to try. Anyway, you'll definitely be improving on the quality of what Irish you have by leaps and bounds.